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Ch. 21 - Carboxylic Acid Derivatives
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo
Capitolo 21, Problema 63a

The structures of four useful polymers are shown, together with some of their best-known products. In each case,
(i) Determine the kind of polymer (polyamide, polyester, etc.).
(ii) Draw the structures of the monomers that would be released by complete hydrolysis.
(iii) Suggest what monomers or stable derivatives of the monomers might be used to make these polymers.
(a)

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Step 1: Identify the type of polymer. The structure shown contains ester functional groups (-COO-) in the repeating unit, indicating that this polymer is a polyester.
Step 2: Determine the monomers released by complete hydrolysis. Hydrolysis of the ester bonds will yield two types of monomers: (i) a diol (HO-CH2-CH2-OH) and (ii) a dicarboxylic acid (HOOC-C6H4-COOH).
Step 3: Draw the structures of the monomers. The diol is ethylene glycol (HO-CH2-CH2-OH), and the dicarboxylic acid is terephthalic acid (HOOC-C6H4-COOH). These are the building blocks released upon hydrolysis.
Step 4: Suggest monomers or stable derivatives used to make the polymer. Ethylene glycol and terephthalic acid can be directly used to synthesize the polymer. Alternatively, dimethyl terephthalate (CH3OOC-C6H4-COOCH3) can be used as a stable derivative of terephthalic acid.
Step 5: Explain the polymerization process. The polymer is formed through a condensation reaction between ethylene glycol and terephthalic acid (or its derivative), where water is eliminated as a byproduct during the formation of ester bonds.

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Types of Polymers

Polymers can be classified into various types based on their chemical structure and the nature of their monomers. Common types include polyamides, which are formed from amino acids, and polyesters, which are derived from diols and dicarboxylic acids. Understanding the type of polymer is crucial for predicting its properties and applications.
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Hydrolysis of Polymers

Hydrolysis is a chemical process that involves the breakdown of polymers into their monomeric units through the addition of water. This reaction is essential for understanding how polymers can be synthesized and degraded, as well as for determining the monomers released during complete hydrolysis, which is a key part of the question.
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Introduction to Polymers Example 2

Monomer Structures

Monomers are the basic building blocks of polymers, and their structures dictate the properties of the resulting polymer. Identifying the monomers used to create a polymer involves analyzing the repeating units and functional groups present in the polymer structure. This knowledge is vital for suggesting potential monomers or derivatives for polymer synthesis.
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